The Red Caboose
by Tidia
Summary: Sam's upset because he has a test and the hunt is taking time away from studying.  Dean thinks it's time for Sam to relax, and has the perfect solution.  Slight mention of The Brotherhood.


The Red Caboose

By: Tidia

Disclaimer: Supernatural belongs to Kripke. The Brotherhood was created by Ridley C. James.

Notes: The Brotherhood is only slightly mentioned because of the usage of Caleb. This is based on a true story. LOL. I was inspired. Mog wanted in on this story and betaed it for me. Ridley had a sneak peek too. I hope you all enjoy a break from the angst. So, I would suggest reading Black Bras and Strappy High Heeled Shoes because the title of this fic comes from that one, and now it is Sam's turn to have his first time.

Sam sighed loudly, again. After the second time, Dean had turned up the volume on the radio, but still he heard the most recent one. He had been expecting it.

"I'm driving as fast as I can, Sam," Dean said, with patience beyond his 21 years. If his brother were normal, then he'd want to go to the nearest bar, use the fake ID that said he was of age, and drink.

But was Saturday night and Sam wanted to go home and study for a test.

"It's important," Sam whined, "I'm not getting anything done this way." An open chemistry book rested on one knee and a notebook lay across the other. He held a flashlight in one hand and a pen in the other.

Dean had tried to quiz him, remembering as much as he could about high school chemistry while concentrating on the demise of the Assante's poltergeist. Sam hadn't appreciated his efforts. Was it his fault he found stoichiometry easy?

"You need to relax, man. You're going to do fine." Dean shifted in the driver seat, glancing up at the green interstate sign: Soso, Mississippi, 60 miles. He hadn't realized they were so close. Dean glanced over at his brother with a smile. The proximity to Soso provided an opportunity that was time to take. He pulled out his cellphone and Sam released another exasperated sigh at the sound of the touch tone.

"Damien, where you at?" Dean asked before the older hunter uttered little more than a greeting.

"Hey, haven't heard from you in awhile too," Caleb replied with annoyance. "I'm in Alabama."

Dean nodded. Perfect timing, it was a sign. "I'm in Mississippi. An hour away from the Red Caboose, in fact."

Caleb laughed, knowing exactly what was going to happen tonight. They were building memories. "It's about time, Deuce. I can be there in two hours."

"Hell, yeah." Dean shook his head as he noticed his brother bending his lanky frame over the book, trying to absorb the words by being closer to them.

"Don't forget to give him the speech," Caleb reminded Dean.

Dean smiled. He had been fifteen his first time at the Red Caboose after Caleb's strappy high heeled shoes and black bra speech. That information still held true. "See you soon."

"Where are we going?" Sam sounded exactly like their father at that moment.

The older Winchester mimicked the same tone. "I think it's time you played in the big leagues, Sam."

Sam tapped his pen nervously against the book. "What are you talking about?"

Dean sighed. "A man has needs, Sammy, and sometimes those needs can't be satisfied by some old issues of Playboy, Hustler and Penthouse." Dean was aware of his younger brother's stash. He had, in fact, given him most of the magazines. "Bro, you need to get laid."

"I am? What? No." The book, notebook, pen and flashlight fell to the floorboard. The beam of light caught Sam's scared face.

Dean was amused by his brother's reaction and, in true sibling form, laughed. "You saving yourself for marriage? Please don't tell me you believe Pastor Jim?"

"No, I mean, Dean. . ." Sam stuttered, turning red. He glanced down at the flashlight, snatched it up and turned it off to save himself any further embarrassment.

"This is my job as big brother, unless you want Dad to take you— 'cause that's never going to happen." Dean snorted. John Winchester rathered his sons not get involved with women or fun in general.

"Dad? God. No." Sam shook his head, his hair falling into his face, he pushed it away.

"That's what I thought." Dean reached out and squeezed his brother's shoulder, then gestured to the dashboard. "Open the glove box. You're going to need them."

Sam was flappable. Dean watched as his brother picked up a condom by the corner.

"Dean, I don't . . ."

Although Dean shouldn't enjoy his brother's discomfiture, he did. There were too few opportunities with Sam without him being sullen or their father intervening. "Take three."

Sam heeded the advice and took a few more condoms, stuffing them into his pocket.

"I am going to give you some advice. . ." And Dean passed along what Caleb had told him when he was fifteen and in the parking lot of the Red Caboose.

"You're telling me it's about clothing? Shoes and a bra? What about paying attention to what she says?" Sam scoffed.

Caleb would be unhappy to learn that Sam had dismissed his counsel. "Not important." Dean frowned. The youngest Winchester was analyzing casual sex to the point where he would remain a virgin forever. "We're talking about a one night stand here, Sammy, not the future Mrs. Sam Winchester."

Sam nodded. What surprised Dean was that Sam wasn't protesting, at least not too much.

"I should really be studying." Sam picked up the discarded books and notebook.

"It'll be an hour before we get there. Study up."

The flashlight flickered on once more, the books were placed back in position, but Dean noticed the page never moved.

They pulled into the Red Caboose and Dean grinned. Not much had changed, except there were a few more cars in the lot because it was the weekend. Sam got out of the Impala and wiped his hands on his jeans.

"Don't forget to use the ID." Dean reminded his brother as he corralled him towards the door. Sam's false identification wasn't checked and Dean pointed to a table in the corner for Sam to take while he got a pitcher of beer.

He returned, balancing the pitcher and two mugs. Sam was slouched at the table trying to minimize his height. The teen exuded gawkiness.

"Dude, straighten up, and look happy," Dean mumbled, and pushed the pitcher towards his brother. Dean scanned the room, catching the eye of a brunette who gave him a come hither smile before looking away. She was with another girl who was attractive and, Dean was pleased to see, wearing strappy high heeled shoes that tied around her ankles. Perfect.

"Stay here. Be alert. Caleb should be here soon. I'm going to do some recon." Sam gave his brother a nod and returned to the beer.

* * *

Caleb slipped in the door of the Red Caboose. He took in the ambience. The same uneven pine floor, old jukebox, scarred bar and picture of a tractor on the wall. The music had moved up a decade, but was still a decade behind. Dean was talking to two women, and he gave the younger hunter a nod. Caleb found Sam in the corner with an empty pitcher of beer.

He lifted a hand and caught the bartender's attention. "Tequila." He put two fingers for two shots. Caleb slipped into the seat across from Sam. "Heard tonight was the big night."

"Shut up." Sam groused.

The kid was evidently nervous. A waitress slipped the shots on the table with a smile for Caleb. "This is a happy place." Reaves sighed.

"It's a crummy bar, not Disney World, Caleb." Sam fingered the top of the shot glass.

"But it is." Reaves knocked back the shot and let it settle for a moment before explaining his answer. "I took your brother here when he was fifteen."

"Fifteen? Does Dad know?" Sam's eyes grew wide.

"It's not like we had his blessing, Runt." Caleb put his hands up in a calming gesture. Sam was wired. "I got us two rooms at the General Lee Motel. Under the names Truckee and Likely."

Sam rolled his eyes. "You are so weird."

"You guys pick rock stars and I pick strange city names." It helped him with geography and getting around the country. His method was at least useful. "Who's weirder?"

"What state?" Sam asked as he rubbed the back of his neck.

"This week is California." It was a big state with lots of strange town names. Caleb gestured with his chin. Sam turned around to see Dean returning to the table.

The older Winchester took the empty seat next to his brother. He lifted his fist to Caleb, who tapped it with his own fist in greeting. "So were you a good wingman?" asked Caleb.

"Dude, I'm Maverick, not Goose. Heather has a sister." Dean turned around and grinned at the smiling blonde. He waved at the brunette, then turned back and rubbed his brother's hair. "And she wants you."

"What? Dean, what did you say?" Sam blushed.

"Drink." Dean pushed the shot towards his brother.

Sam took the drink and Caleb watched the younger hunter pale. "You aren't going to throw up are you?"

"Shut up," Dean answered and lifted his brother to his feet. "He's a Winchester." Dean gave Sam a slight push forward. "Just go over there, and have fun."

"Guess he's not going to be our little boy forever," Caleb commented as Sam made his way towards the brunette. The blonde, her sister, excused herself and gestured to Dean that she was heading towards the bathroom.

Dean and Caleb watched the twosome. She would bob her head and Sam would nod. "He's talking to her." Dean groaned and placed his head on the table.

"Not everyone goes in for the kill. Let him find his own way." Caleb smiled. "Plus I'll send over a few rounds of drinks to keep things moving."

"Dude, he has to be able to perform." Dean lifted his head. "He's over 17. It was time. Right?"

Reaves nodded. "You did good, Deuce. You know your brother is a late bloomer. Who knows what would have happened? He may have actually taken Pastor Jim's advice."

"He thought your speech sucked." Dean rested back in the chair.

"My speech does not suck." Caleb was not surprised, Sam was a thinker. He liked to analyze a situation. "Did wonders for you."

"That it did." Dean raised his eyebrows up and down. "You going home alone tonight?"

"Not likely… with Miss Lisa." He turned to face a curly haired brunette at the bar, who was teasing a straw with her mouth. She met his glance. "What she wants to do to me. . . ."

"Isn't that using your powers for evil?"

Pastor Jim was always pressing the issue of being responsible, and how his abilities were a good thing. But, responsibility had to be tempered, and sometimes used to benefit oneself. "I was evidently blessed with these abilities, might as well benefit from them, and my classic good looks don't hurt either."

Dean laid his hands down flat on the table. "You got style, Damien; I'll say that about you."

Heather and Lisa helped pass the time for the two hunters. Dean kept glancing back to check on his brother. Things finally progressed when Heather's sister, Amanda, grabbed Sam by the hand and led him out the door. Reaves caught the other hunter's attention.

"I'll catch up with you guys later," Sam said as he passed by the table. His arm was looped over Amanda's shoulder and Caleb didn't know if the girl was supporting most of the youngest Winchester's lanky frame.

"Okay, Sammy." Dean lifted his glass in salute.

* * *

Sam dreamily headed down the hallway of the General Lee Motel after an early morning breakfast. Amanda had dropped him off with a lingering kiss. He could still taste a hint of strawberry gloss as he knocked on one of the hotel rooms There was no answer, instead the door of the neighboring room opened. Dean popped his head out and studied his brother with a grin.

"We were getting worried."

Sam confidently strode into the room, holding a cage by his side. Caleb sat on one of the beds, a Styrofoam container sat to one side.

"So-" Caleb pointed to the cage. "What've you got there?"

"A hamster." Sam grinned, lifted the cage and poked a finger through the cage. The animal responded with a squeak. "I bought it. His name is Pedro."

"You bought it?" Dean studied the hamster, then his brother, returned his gaze to the hamster, then finally sat down next to Caleb. "Before or after. . .Tell me you didn't. . ."

Dean and Caleb's eyes were wide, staring at him. He looked at Pedro, and his mouth dropped open, stunned. Truly, he wondered about the guttural thoughts of the older hunters. "God! No. No!"

Dean was relieved, but speechless. He waved his arm in front of Reaves. "I think what your brother is trying to ask is - how your first time leads to a parting gift of a rodent?"

Sam rested Pedro's cage on the television, careful to make sure it wouldn't tip over. It seemed sturdy enough. "Don't know why the lady sold it to me. Really, I was in no condition to take care of an animal." He kept one hand resting on the cage.

"Drunk hamster buying?" Dean said, his voice rising.

"Right. At an all night pet store." Sam nodded eagerly. He had always wanted a pet, and it seemed like a good idea and a perfect opportunity at the time. "Amanda said she really liked hamsters. We were walking back to Heather's place, and I saw this pet store…"

Caleb was laughing a 'hands resting on knees, bent over trying hard to take in a deep breath' kind of laugh.

"Stop laughing, Damien." Dean shoved Reaves's shoulder. "This is embarrassing. Please tell me you did the deed, please?"

Sam was not going to confirm what had happened last night. Sam had decided to be different from Dean and Caleb and not speak about his conquests. He respected Amanda. He looked at the other hunters and shrugged his shoulders. It wasn't embarrassing at all. Everything was as it should be. "Amanda likes hamsters. She suggested the name." Sam happily went along with it, in fact , he'd gone along with everything she suggested.

Dean stood up. "It's not coming into the Impala."

"I can't believe you named it." Caleb was still trying to control his laughing fits. "Deuce, I told you that you should have allowed Sammy a pet growing up. . ."

"If Amanda likes hamsters, we'll drop it off then." Dean ignored his friend, picked up the cage and placed it in Sam's hands.

"I can do it," Sam volunteered, "while you two pack up." Dropping off Pedro would probably lead to something else, and Sam didn't want his brother waiting outside.

"You sure, what about that test on Monday?"

Sam had forgotten about the chemistry test. "I'll cram on the ride home."

Dean stepped back and appraised his brother. He tossed the Impala's keys at Sam. "Make it quick. Take what you need from the glove box, but after this you buy your own."

Sam didn't turn around. He opened the door, but could still hear Caleb through the door.

"Dude, I am so putting this in my hunter's journal so that future generations can be awed by Sam Winchester."

"Awed is right. He invented a new drunken activity—hamster buying, go figure."

Sam lifted the cage so the hamster was at eye level. "Maybe we should have named you Lucky."

The end


End file.
